Hydrochloric Acid → HCID 13851158, compound

HRID 364981Notes

Reaction equation

HRID 364981 reaction equation
[ClH:1].[C:2]1([CH:8]2[O:13][CH2:12][CH2:11][NH:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]([CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](=O)[CH3:28])=[CH:22][CH:21]=1)([O:16][CH3:17])=[O:15].C([BH3-])#N.[Na+].Cl>CO.ClCCl.C(OCC)C>[ClH:1].[CH3:17][O:16][C:14](=[O:15])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH:27]([N:10]2[CH2:11][CH2:12][O:13][CH:8]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9]2)[CH3:28])=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 123435392-Phenylmorpholine--hydrogen chloride (1/1)HCID 13851156Methyl 2-(4-(2-oxopropyl)phenoxy)acetate

Product 1

HCID 13851158HCID 13851158, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-phenylmorpholine hydrochloride (6.05 g), 1-(4-carbomethoxymethoxyphenyl)propan-2-one (6.63 g) and sodium cyanoborohydride (1.61 g) in methanol (100 ml) was stirred at room temperature for 22 hours. The solvent was removed under reduced pressure and aqueous sodium bicarbonate solution added to the residue and extracted with dichloromethane (×2). The extracts were washed with aqueous sodium bicarbonate, dried over anhydrous magnesium sulphate, filtered and the filtrate evaporated to dryness to give an oil. Chromatography on silica gel in 0→7% methanol in dichloromethane gave an oil which was dissolved in diethyl ether and treated with an ethereal solution of hydrogen chloride. Evaporation to dryness and trituration of the residue with ethyl acetate gave a solid. Recrystallisation of this solid gave the title compound, m.p. 187°-190° C. (methanol-ethyl acetate), of analytical purity.

Workup

  1. customThe solvent was removed under reduced pressure and aqueous sodium bicarbonate solution
  2. additionadded to the residue
  3. extractionextracted with dichloromethane (×2)
  4. washThe extracts were washed with aqueous sodium bicarbonate
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customthe filtrate evaporated to dryness
  8. customto give an oil
  9. customEvaporation to dryness and trituration of the residue with ethyl acetate
  10. customgave a solid
  11. customRecrystallisation of this solid

Sources & evidence

ORD record
ord-43274329a32c4409825b14d676b0fd11
Source dataset
uspto-grants-1986_08
Patent number
US04607033

Reaction notes

Loading…